Asymmetric Direct Vinylogous Aldol Reaction of Unactivated γ-Butenolide to Aldehydes

被引：55

作者：

Yang, Yang ^{[1
]}

Zheng, Ke ^{[1
]}

Zhao, Jiannan ^{[1
]}

Shi, Jian ^{[1
]}

Lin, Lili ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期

基金：

中国国家自然科学基金;

关键词：

NAFUREDIN-GAMMA; BRONSTED ACID; MANNICH-TYPE; 2-(TRIMETHYLSILYLOXY)FURAN; 2-TRIMETHYLSILYLOXYFURAN; ORGANOCATALYSIS; LAMBERTELLOLS; DERIVATIVES; ACTIVATION; CATALYSIS;

D O I：

10.1021/jo100946d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric direct vinylogous aldol reaction of unactivated gamma-butenolide with aldehydes has been developed, giving the corresponding 5-(1'-hydroxy)butenolide derivatives in high yields (up to 93%) and enantioselectivities (up to 83% ee) under mild conditions.

引用

页码：5382 / 5384

页数：3

共 50 条

[21] Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding
Villano, Rosaria
Acocella, Maria Rosaria
Massa, Antonio
Palombi, Laura
Scettri, Arrigo
TETRAHEDRON, 2009, 65 (28) : 5571 - 5576
[22] Direct catalytic asymmetric aldol reaction
Yoshikawa, N
Yamada, YMA
Das, J
Sasai, H
Shibasaki, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) : 4168 - 4178
[23] The direct catalytic asymmetric aldol reaction
Trost, Barry M.
Brindle, Cheyenne S.
CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) : 1600 - 1632
[24] The direct catalytic asymmetric aldol reaction
Alcaide, B
Almendros, P
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (10) : 1595 - 1601
[25] Asymmetric Vinylogous Aldol Reaction of α-ketoesters with 3-alkylidene oxindoles
Kumar, Krishna
Jaiswal, Manish K.
Singh, Ravi P.
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4136 - 4140
[26] Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt
Singh, Ravi P.
Foxman, Bruce M.
Deng, Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (28) : 9558 - 9560
[27] Asymmetric Vinylogous Mukaiyama Aldol Reaction of Aldehyde-Derived Dienolates
Gieseler, Marc T.
Kalesse, Markus
ORGANIC LETTERS, 2011, 13 (09) : 2430 - 2432
[28] Tertiary Amine Promoted Asymmetric Aldol Reaction of Aldehydes
Gut, Bartosz
Mlynarski, Jacek
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5075 - 5078
[29] Organocatalytic Asymmetric Vinylogous Aldol Reactions
Bisai, Vishnumaya
SYNTHESIS-STUTTGART, 2012, 44 (10): : 1453 - 1463
[30] Direct Vinylogous Aldol Reaction Triggered by Tetrabutylammonium Fluoride: A Highly Regioselective and Diastereoselective Addition of Cyclic β-Haloenals to Aromatic Aldehydes
Zhang, Jingli
Gu, Lianghu
Gong, Yuefa
SYNLETT, 2012, (03) : 468 - 472

← 1 2 3 4 5 →